JPH0813820B2 - ７β−（置換）アミノ−３−置換セフアロスポラン酸類およびエステル類 - Google Patents

７β−（置換）アミノ−３−置換セフアロスポラン酸類およびエステル類

Info

Publication number: JPH0813820B2
Authority: JP; Japan
Prior art keywords: amino; methyl; thia; azabicyclo; oxo
Prior art date: 1986-07-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP62170845A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6388188A (ja

Inventor

ビング・ジツク・リー

ウイリアム・ビンセント・カラン

Original Assignee

アメリカン・サイアナミド・カンパニ−

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-07-08

Filing date

1987-07-08

Publication date

1996-02-14

1987-07-08 Application filed by アメリカン・サイアナミド・カンパニ− filed Critical アメリカン・サイアナミド・カンパニ−

1988-04-19 Publication of JPS6388188A publication Critical patent/JPS6388188A/ja

1996-02-14 Publication of JPH0813820B2 publication Critical patent/JPH0813820B2/ja

2011-02-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000002253 acid Substances 0.000 title description 5
150000002148 esters Chemical class 0.000 title description 2
150000007513 acids Chemical class 0.000 title 1
-1 monosubstituted phenyl Chemical group 0.000 claims description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 26
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 22
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
KAQQVFLJKNKXNS-MLGOLLRUSA-N (6r,7r)-3-[(5-methylthiadiazol-4-yl)sulfanylmethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1N=NC(SCC=2CS[C@H]3N(C([C@H]3NC(=O)CC=3SC=CC=3)=O)C=2C(O)=O)=C1C KAQQVFLJKNKXNS-MLGOLLRUSA-N 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
125000006267 biphenyl group Chemical group 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000006260 foam Substances 0.000 description 6
229930186147 Cephalosporin Natural products 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229940124587 cephalosporin Drugs 0.000 description 5
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
150000001780 cephalosporins Chemical class 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
239000008272 agar Substances 0.000 description 2
NZDJTVSTIFYISQ-UHFFFAOYSA-N iodomethyl acetate Chemical compound CC(=O)OCI NZDJTVSTIFYISQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
239000008188 pellet Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
BHAVPUWJABXCHG-UHFFFAOYSA-N 5-(4-tert-butylphenyl)thiadiazole-4-thiol Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=C(S)N=NS1 BHAVPUWJABXCHG-UHFFFAOYSA-N 0.000 description 1
XPLRQIJQOOBETR-UHFFFAOYSA-N 5-ethylthiadiazole-4-thiol Chemical compound CCC=1SN=NC=1S XPLRQIJQOOBETR-UHFFFAOYSA-N 0.000 description 1
ACDCQYDCRGAKNQ-UHFFFAOYSA-N 5-phenylthiadiazole-4-thiol Chemical compound N1=NSC(C=2C=CC=CC=2)=C1S ACDCQYDCRGAKNQ-UHFFFAOYSA-N 0.000 description 1
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
ZTGRDIXGECURAY-UHFFFAOYSA-N CC(I)C(C)OC(O)=O Chemical compound CC(I)C(C)OC(O)=O ZTGRDIXGECURAY-UHFFFAOYSA-N 0.000 description 1
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
BUKJBGNGPQXFTH-UHFFFAOYSA-N benzhydryl 2-methyloct-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C(C)=CCCCCC)C1=CC=CC=C1 BUKJBGNGPQXFTH-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010586 diagram Methods 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
JJJPTTANZGDADF-UHFFFAOYSA-N thiadiazole-4-thiol Chemical compound SC1=CSN=N1 JJJPTTANZGDADF-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP62170845A 1986-07-08 1987-07-08 ７β−（置換）アミノ−３−置換セフアロスポラン酸類およびエステル類 Expired - Lifetime JPH0813820B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88299686A	1986-07-08	1986-07-08
US882996		1986-07-08

Publications (2)

Publication Number	Publication Date
JPS6388188A JPS6388188A (ja)	1988-04-19
JPH0813820B2 true JPH0813820B2 (ja)	1996-02-14

Family

ID=25381778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62170845A Expired - Lifetime JPH0813820B2 (ja)	1986-07-08	1987-07-08	７β−（置換）アミノ−３−置換セフアロスポラン酸類およびエステル類

Country Status (14)

Country	Link
EP (1)	EP0252473A3 (da)
JP (1)	JPH0813820B2 (da)
KR (1)	KR950008320B1 (da)
AU (1)	AU599676B2 (da)
CA (1)	CA1284147C (da)
DK (1)	DK349687A (da)
FI (1)	FI88042C (da)
HU (1)	HU198070B (da)
IL (1)	IL83119A (da)
NO (1)	NO171726C (da)
NZ (1)	NZ220995A (da)
PH (1)	PH24324A (da)
PT (1)	PT85276B (da)
ZA (1)	ZA874941B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4803280A (en) *	1986-07-08	1989-02-07	American Cyanamid Company	Substituted 1,2,3-thia-diazole-4-thiolates
GB2517979A (en) *	2013-09-06	2015-03-11	Taylor Kerr Couplings Ltd	Pipe coupling with dynamic axial restraint system

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4399132A (en) *	1980-08-11	1983-08-16	American Cyanamid Company	7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof
US4914091A (en) *	1984-04-02	1990-04-03	American Cyanamid Company	Esters of cephalosporin derivitives
EP0168177A3 (en) *	1984-06-28	1987-04-01	Pfizer Limited	Cephalosporin antibiotics

1987
- 1987-07-06 EP EP87109702A patent/EP0252473A3/en not_active Ceased
- 1987-07-07 DK DK349687A patent/DK349687A/da not_active Application Discontinuation
- 1987-07-07 AU AU75311/87A patent/AU599676B2/en not_active Ceased
- 1987-07-07 ZA ZA874941A patent/ZA874941B/xx unknown
- 1987-07-07 PT PT85276A patent/PT85276B/pt not_active IP Right Cessation
- 1987-07-07 FI FI872999A patent/FI88042C/fi not_active IP Right Cessation
- 1987-07-07 NO NO872825A patent/NO171726C/no unknown
- 1987-07-08 HU HU873079A patent/HU198070B/hu not_active IP Right Cessation
- 1987-07-08 PH PH35510A patent/PH24324A/en unknown
- 1987-07-08 KR KR1019870007330A patent/KR950008320B1/ko not_active Expired - Lifetime
- 1987-07-08 JP JP62170845A patent/JPH0813820B2/ja not_active Expired - Lifetime
- 1987-07-08 NZ NZ220995A patent/NZ220995A/xx unknown
- 1987-07-08 IL IL83119A patent/IL83119A/xx not_active IP Right Cessation
- 1987-07-08 CA CA000541586A patent/CA1284147C/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA874941B (en)	1988-02-24
KR890002181A (ko)	1989-04-08
FI88042C (fi)	1993-03-25
PH24324A (en)	1990-05-29
IL83119A0 (en)	1987-12-31
FI872999A7 (fi)	1988-01-09
EP0252473A3 (en)	1989-07-05
HUT45070A (en)	1988-05-30
EP0252473A2 (en)	1988-01-13
FI88042B (fi)	1992-12-15
NO872825L (no)	1988-01-11
PT85276A (en)	1987-08-01
AU599676B2 (en)	1990-07-26
JPS6388188A (ja)	1988-04-19
NO171726B (no)	1993-01-18
NO872825D0 (no)	1987-07-07
AU7531187A (en)	1988-01-14
HU198070B (en)	1989-07-28
FI872999A0 (fi)	1987-07-07
DK349687A (da)	1988-01-09
NO171726C (no)	1993-04-28
IL83119A (en)	1993-04-04
NZ220995A (en)	1989-10-27
KR950008320B1 (ko)	1995-07-27
CA1284147C (en)	1991-05-14
PT85276B (pt)	1990-03-30
DK349687D0 (da)	1987-07-07

Publication	Publication Date	Title
EP0251299B1 (en)	1994-08-31	Cephalosporin compounds, processes for their preparation and antibacterial agents
FI66618C (fi)	1984-11-12	Foerfarande foer framstaellning av terapeutiskt verkande 7-(2-(2-aminotiazol-4-yl)-2-(syn)-metoxi-iminoacetamido-cefalosporinderivat
KR20030078882A (ko)	2003-10-08	티아졸릴 아세트산의 신규 티오에스테르 유도체 및세팔로스포린 화합물의 제조에서 그의 용도
Lattrell et al.	1988	Synthesis and structure-activity relationships in the cefpirome series I. 7-[2-(2-Aminothiazol-4-yl)-2-(Z)-oxyiminoacetamido]-3-[(substituted-1-pyridinio) methyl]-ceph-3-em-4-carboxylates
JPH0333712B2 (da)	1991-05-20
GB2051810A (en)	1981-01-21	Cephalosporin compounds processes for their preparation and antibacterial drugs containing them
US4971962A (en)	1990-11-20	Cephalosporin compounds
US3637678A (en)	1972-01-25	Delta-2 cephalosporin compounds
JPS62491A (ja)	1987-01-06	３−（置換）プロペニルアミノチアゾリルセフアロスポラン酸およびそのエステル
US4874856A (en)	1989-10-17	3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof
JPH0813820B2 (ja)	1996-02-14	７β−（置換）アミノ−３−置換セフアロスポラン酸類およびエステル類
JPH0613530B2 (ja)	1994-02-23	セフエム化合物
JP2529093B2 (ja)	1996-08-28	セファロスポリン中間体の製造方法
US4927922A (en)	1990-05-22	7β-(substituted)amino-3-substituted cephalosporanic acids and esters
JP2549494B2 (ja)	1996-10-30	ピリドンイソオキサゾールセフェム化合物及びその製造方法
JPH08151386A (ja)	1996-06-11	複素環エチルチオセフェム化合物、その製造法および抗菌組成物
KR0157589B1 (ko)	1998-11-16	신규 세팔로스포린계 항생제 및 이의 제조방법
JPS60237090A (ja)	1985-11-25	セフエム化合物
JP2567799B2 (ja)	1996-12-25	カルボキシアルケン酸及びその誘導体
JPS60260584A (ja)	1985-12-23	セフアロスポリン誘導体
JPH0859669A (ja)	1996-03-05	セフェム化合物、その製造法及び剤
WO1998058933A1 (en)	1998-12-30	Cephalosporin compounds, use thereof and intermediate compounds of the same
JP2617618B2 (ja)	1997-06-04	セフアロスポリン誘導体
EP0481441A2 (en)	1992-04-22	Novel cephem compounds, their preparation processes and antibacterial agents
JPS63152386A (ja)	1988-06-24	新規なセファロスポリン化合物